diff --git a/alerting/src/main/kotlin/org/opensearch/alerting/DocumentLevelMonitorRunner.kt b/alerting/src/main/kotlin/org/opensearch/alerting/DocumentLevelMonitorRunner.kt
index 27a3cdf4f..0164aa00e 100644
--- a/alerting/src/main/kotlin/org/opensearch/alerting/DocumentLevelMonitorRunner.kt
+++ b/alerting/src/main/kotlin/org/opensearch/alerting/DocumentLevelMonitorRunner.kt
@@ -121,17 +121,6 @@ class DocumentLevelMonitorRunner : MonitorRunner() {
                 throw IndexNotFoundException(docLevelMonitorInput.indices.joinToString(","))
             }
 
-            if (monitor.deleteQueryIndexInEveryRun == true &&
-                monitorCtx.docLevelMonitorQueries!!.docLevelQueryIndexExists(monitor.dataSources)
-            ) {
-                val ack = monitorCtx.docLevelMonitorQueries!!.deleteDocLevelQueryIndex(monitor.dataSources)
-                if (!ack) {
-                    logger.error(
-                        "Deletion of concrete queryIndex:${monitor.dataSources.queryIndex} is not ack'd! " +
-                            "for monitor ${monitor.id}"
-                    )
-                }
-            }
             monitorCtx.docLevelMonitorQueries!!.initDocLevelQueryIndex(monitor.dataSources)
             monitorCtx.docLevelMonitorQueries!!.indexDocLevelQueries(
                 monitor = monitor,
diff --git a/alerting/src/main/kotlin/org/opensearch/alerting/util/DocLevelMonitorQueries.kt b/alerting/src/main/kotlin/org/opensearch/alerting/util/DocLevelMonitorQueries.kt
index fae53879f..59ddea360 100644
--- a/alerting/src/main/kotlin/org/opensearch/alerting/util/DocLevelMonitorQueries.kt
+++ b/alerting/src/main/kotlin/org/opensearch/alerting/util/DocLevelMonitorQueries.kt
@@ -358,7 +358,8 @@ class DocLevelMonitorQueries(private val client: Client, private val clusterServ
                 monitorMetadata,
                 updatedIndexName,
                 sourceIndexFieldLimit,
-                updatedProperties
+                updatedProperties,
+                indexTimeout
             )
 
             if (updateMappingResponse.isAcknowledged) {
@@ -488,7 +489,8 @@ class DocLevelMonitorQueries(private val client: Client, private val clusterServ
         monitorMetadata: MonitorMetadata,
         sourceIndex: String,
         sourceIndexFieldLimit: Long,
-        updatedProperties: MutableMap<String, Any>
+        updatedProperties: MutableMap<String, Any>,
+        indexTimeout: TimeValue
     ): Pair<AcknowledgedResponse, String> {
         var targetQueryIndex = monitorMetadata.sourceToQueryIndexMapping[sourceIndex + monitor.id]
         if (
@@ -552,9 +554,48 @@ class DocLevelMonitorQueries(private val client: Client, private val clusterServ
                     }
                 }
             } else {
-                log.debug("unknown exception during PUT mapping on queryIndex: $targetQueryIndex")
-                val unwrappedException = ExceptionsHelper.unwrapCause(e) as Exception
-                throw AlertingException.wrap(unwrappedException)
+                // retry with deleting query index
+                if (monitor.deleteQueryIndexInEveryRun == true) {
+                    try {
+                        log.error(
+                            "unknown exception during PUT mapping on queryIndex: $targetQueryIndex, " +
+                                "retrying with deletion of query index",
+                            e
+                        )
+                        if (docLevelQueryIndexExists(monitor.dataSources)) {
+                            val ack = monitorCtx.docLevelMonitorQueries!!.deleteDocLevelQueryIndex(monitor.dataSources)
+                            if (!ack) {
+                                log.error(
+                                    "Deletion of concrete queryIndex:${monitor.dataSources.queryIndex} is not ack'd! " +
+                                        "for monitor ${monitor.id}"
+                                )
+                            }
+                        }
+                        initDocLevelQueryIndex(monitor.dataSources)
+                        indexDocLevelQueries(
+                            monitor = monitor,
+                            monitorId = monitor.id,
+                            monitorMetadata,
+                            indexTimeout = indexTimeout
+                        )
+                    } catch (e: Exception) {
+                        log.error(
+                            "Doc level monitor ${monitor.id}: unknown exception during " +
+                                "PUT mapping on queryIndex: $targetQueryIndex",
+                            e
+                        )
+                        val unwrappedException = ExceptionsHelper.unwrapCause(e) as Exception
+                        throw AlertingException.wrap(unwrappedException)
+                    }
+                } else {
+                    log.error(
+                        "Doc level monitor ${monitor.id}: unknown exception during " +
+                            "PUT mapping on queryIndex: $targetQueryIndex",
+                        e
+                    )
+                    val unwrappedException = ExceptionsHelper.unwrapCause(e) as Exception
+                    throw AlertingException.wrap(unwrappedException)
+                }
             }
         }
         // We did rollover, so try to apply mappings again on new targetQueryIndex
diff --git a/sample-remote-monitor-plugin/src/main/java/org/opensearch/alerting/SampleRemoteMonitorRestHandler.java b/sample-remote-monitor-plugin/src/main/java/org/opensearch/alerting/SampleRemoteMonitorRestHandler.java
index a8f384cb6..9875ef55f 100644
--- a/sample-remote-monitor-plugin/src/main/java/org/opensearch/alerting/SampleRemoteMonitorRestHandler.java
+++ b/sample-remote-monitor-plugin/src/main/java/org/opensearch/alerting/SampleRemoteMonitorRestHandler.java
@@ -94,7 +94,7 @@ protected RestChannelConsumer prepareRequest(RestRequest restRequest, NodeClient
                                 "id", null)), trigger1Serialized)),
                 Map.of(),
                 new DataSources(),
-                true,
+                false,
                 "sample-remote-monitor-plugin"
         );
         IndexMonitorRequest indexMonitorRequest1 = new IndexMonitorRequest(
@@ -155,7 +155,7 @@ public void onFailure(Exception e) {
                     List.of(),
                     Map.of(),
                     new DataSources(),
-                    true,
+                    false,
                     "sample-remote-monitor-plugin"
             );
             IndexMonitorRequest indexMonitorRequest2 = new IndexMonitorRequest(
@@ -239,7 +239,7 @@ public void onFailure(Exception e) {
                                     "id", null)), trigger1Serialized)),
                     Map.of(),
                     new DataSources(),
-                    true,
+                    false,
                     "sample-remote-monitor-plugin"
             );
             IndexMonitorRequest indexDocLevelMonitorRequest = new IndexMonitorRequest(